Holiday Winter Weekend in Portsmouth, New Hampshire

The historic seaside town of Portsmouth, New Hampshire, shines especially bright at Christmastime.

By Yankee Magazine

Oct 20 2022


A 35-foot Christmas tree anchors the downtown holiday scene.

Photo Credit : Michael D. Wilson

By Courtney Hollands

I was gliding around an outdoor skating rink in Portsmouth, New Hampshire, when it hit me: I could be in a Hallmark holiday movie. No, I’m not a high-powered executive with skewed priorities who returns to her hometown only to fall in love with the local artisan hot chocolate maker—I am, in fact, a happily married writer and editor from Boston. Rather, it’s Portsmouth’s charm and the seasonal spirit that permeates every corner of the historic port city at this time of year that gives it an almost cinematic quality.

The open-air museum Strawbery Banke is a hub of yuletide activity, with an outdoor ice rink bustling with skaters of all ages and a historic campus transformed into a winter wonderland.

I had come with my husband, and our stay was brief—just a weekend visit in early December. But between the artfully decorated shop windows, the spontaneous displays of holiday cheer, and the time-honored events in Portsmouth’s annual Vintage Christmas celebration, we left in a holly-jolly state of mind, vowing to return winter after winter.

Scenes from a December weekend in Portsmouth.

We were welcomed to the festive downtown scene by a busker playing “Go Tell It on the Mountain” in Market Square, beneath its 35-foot-tall Christmas tree. The donated spruce’s 2,000 LED lights—switched on just the weekend before, as part of the city’s long-running Illuminated Holiday Parade and Tree Lighting—twinkled against an overcast sky as we browsed the independent boutiques along Congress and Market streets.

Scenes from a December weekend in Portsmouth, including gift ideas at Gus & Ruby Letterpress
Photo Credit : Michael D. Wilson

The stores, surely in contention for New England’s best stretch of holiday shopping, really turn it on after Thanksgiving. The front windows at Gus & Ruby Letterpress were strewn with paper snowflakes, and there was greenery spilling off the shelves. “When we start burning our Christmas candles, it puts people in the mood,” co-owner Samantha Finigan told me. “It’s sort of the hallmark of the season.” Menswear shop Sault NE was similarly decked out with strings of retro rainbow-colored bulbs and evergreen boughs, which, when paired with the “Live Free or Die” sweatshirts and other locally made goods, gave us all the Christmas-y New England feels.

The open-air museum Strawbery Banke is a hub of yuletide activity, with an outdoor ice rink bustling with skaters of all ages and a historic campus transformed into a winter wonderland.

This merry vibe continued at the Strawbery Banke Museum’s Candlelight Stroll, one of the anchor events of Portsmouth’s Vintage Christmas (now in its 18th year, the townwide celebration also features a gingerbread house contest and concerts and shows at the iconic Music Hall and other venues). We walked the outdoor museum’s pathways, talking to costumed role-players and learning how the holidays have evolved over the three centuries of history that Strawbery Banke encompasses. An almost sacred hush enveloped us as we sipped hot cider, sniffed the wafting bonfire smoke, and took in the wintry tableau—the stroll was very much, as Strawbery Banke curator Elizabeth Farish had described it, a “sensory experience.”

Strawbery Banke visitors get a winter warm-up at the cider shed.

In an ideal world (or at least the Hollywood version), our wintery getaway would have included dining by the glow of a roaring fire. But while a blazing hearth wasn’t on offer at the acclaimed bistro Black Trumpet, there were flickering candles, exposed brick and beams, and chef Evan Mallett’s hearty, season-perfect menu. Also warming were the post-dinner black Manhattans and palomas on draft just a few blocks away, at the newish craft cocktail bar The Wilder.

Black Trumpet chef-owner Evan Mallett at his Ceres Street bistro, recently nominated for a James Beard Award for outstanding hospitality.
Refined seafood at Black Trumpet.
Photo Credit : Michael D. Wilson

Afterward, we ventured out into the chilly dark in high spirits, which were raised further by spotting a Santa crossing Congress Street and hearing a bagpiper playing holiday tunes. These characters seemed quite at home on Portsmouth’s lively late-night streets, under lampposts adorned with wreaths. So much so that I half expected passersby to break out in song: Baby, it’s cold outside….

Falling snow gives Market Square just the right holiday feel.

Before leaving town, we returned to Strawbery Banke to lace up for our morning rink reservations at Labrie Family Skate at Puddle Dock Pond. I hadn’t skated in at least a decade, and at first, the blades felt foreign. I started out cautiously, hugging the walls, before picking up speed and looping around the oval—even attempting a twirl as country-music carols crackled over the speakers.

Scenes from a December weekend in Portsmouth.

Equally filled with childlike wonder, my husband remarked that it would be fun for our toddler to try skating there. I remembered then how Strawbery Banke’s Farish had summed up the Candlelight Stroll. “It just sort of makes you happy,” she said. “You can learn about history or you can create your own family traditions.”

The next time we take a Christmas trip to Portsmouth, it will be with our daughter. And it will be magical as any holiday movie.



Cup of Joe: This sweet, sunshine-yellow coffee shop and bar specializes in egg sandwiches and high-octane drinks of all kinds—including an excellent espresso

Assistant Mayor Joanna Kelly takes in the view from her Market Street coffee shop and bar, Cup of Joe.

Black Trumpet: Chef Evan Mallett’s cozy, 15-year-old Ceres Street restaurant showcases Seacoast farm-to-table dining at its finest.

Earth Eagle Brewings: Savor a respite from the shopping crowds with a hoppy saison at this homey brewpub strung with lights and ornaments. Even the mounted bucks have bows.

Elephantine Bakery: Almond croissants. Rosemary focaccia. French drinking chocolate. Don’t be surprised to find a line out the door at Sherif and Nadine Farag’s chic café.

La Maison Navarre: The house-made macarons are the stars, but crepes and quiches are equally superbe, as are the French wines and cheeses.

La Maison Navarre’s house-made macarons.
Photo Credit : Michael D. Wilson

The Wilder: A cool spot for a well-crafted cocktail and brunch (and a top-notch brunch cocktail, of course).


The Sailmaker’s House: A stylish 10-room inn that marries today’s amenities (keyless entry, Matouk linens) with meticulously preserved historic details.

The Sailmaker’s House

The Hotel Portsmouth: The newer sibling of Lark Hotels’ intimate Ale House Inn, offering 32 rooms and suites and Victorian-era charm.

Wentworth by the Sea, A Marriott Hotel & Spa: The grande dame of Portsmouth-area hotels, where snow flurries will surely enhance the postcard-perfect ocean views.


Gus & Ruby Letterpress: Come for the holiday candles, stay for the pithy cards and lovely wrapping paper at this local print studio’s flagship store.

Candles at Gus & Ruby Letterpress

Pickwick’s Mercantile: Staffers sporting fascinators are quick to recommend a tea or handcrafted perfume at this quirky shop, which has a second outpost at Strawbery Banke.

Sault NE: Natty threads share shelf space with rugged totes, rope bracelets, and grooming products at Philip Saul’s menswear emporium.

Treehouse Toys: Colorful, whimsical, and overflowing with games, dolls, puzzles, and books—this is what a toy shop should be. A destination for kids and kids-at-heart alike.


Strawbery Banke Museum: Not only can you learn about Christmases past on a magical Candlelight Stroll through the 10-acre campus, but you can also relive your childhood with a spin around the outdoor skating rink.

Strawbery Banke Museum

The Music Hall:This legendary venue really shines during the Vintage Christmas festivities, partnering with the Ogunquit Playhouse to put on a holiday production and hosting comedy shows and concerts.